Hydrochloric Acid → HCID 20079710, compound

HRID 1654158Notes

Reaction equation

HRID 1654158 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[S:16][CH2:15][CH2:14][CH2:13][S:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([Li])CCC.[Cl:22][CH2:23][CH2:24][CH2:25][N:26]([CH3:44])[CH2:27][C:28]1([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[C:36]([O:42][CH3:43])[CH:35]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.Cl>CCCCCC.O1CCOCC1.O1CCCC1>[ClH:22].[CH3:43][O:42][C:36]1[CH:35]=[C:34]([C:28]2([CH2:27][N:26]([CH3:44])[CH2:25][CH2:24][CH2:23][C:11]3([C:5]4[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=4)[S:12][CH2:13][CH2:14][CH2:15][S:16]3)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]2)[CH:39]=[CH:38][C:37]=1[O:40][CH3:41]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 110105922-(3,4-Dimethoxyphenyl)-1,3-dithianeHCID 20079736HCID 20079736, compoundHCID 178418339Butyllithium

Product 1

HCID 20079710HCID 20079710, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 2.56 g (0.01 mol) of 2-(3,4-dimethoxyphenyl)-m-dithiane in 20 ml of abs. tetrahydrofuran was cooled to -60° in a sulphonation flask while gassing with dry argon and treated dropwise within 15 minutes with 4.68 ml (0.0075 mol) of a solution of butyllithium in hexane, whereby the temperature was held at -60°. Thereafter, the solution was stirred at -20° for 2 hours, then again cooled to -60° and treated dropwise with a solution of 1.70 g (0.005 mol) of N-(3-chloropropyl)-1-(3,4-dimethoxyphenyl)-N-methylcyclohexanemethanamine in 20 ml of abs. tetrahydrofuran. After 16 hours at -20° and 4 hours at room temperature the solution was poured on to ice-water and the mixture was washed three times with ether. The ethereal extracts were dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residual oil was chromatographed on silica gel 60 with toluene/ethyl acetate (8:2 ). After evaporation of the solvent there was obtained a colourless oil which was dissolved in a small amount of abs. dioxan and treated with an excess of hydrogen chloride in abs. dioxan, whereby N-[[1-(3,4-dimethoxyphenyl)cyclohexyl]methyl]-2-(3,4-dimethoxyphenyl)-N-methyl-m-dithiane-2-propanamine hydrochloride was obtained as solid white foam.

Workup

  1. customwas held at -60°
  2. temperatureagain cooled to -60°
  3. waitAfter 16 hours at -20°
  4. washthe mixture was washed three times with ether
  5. dry with materialThe ethereal extracts were dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residual oil was chromatographed on silica gel 60 with toluene/ethyl acetate (8:2 )
  9. customAfter evaporation of the solvent there
  10. customwas obtained a colourless oil which
  11. dissolutionwas dissolved in a small amount of abs

Sources & evidence

ORD record
ord-76c33a0bbfcf408db71bec49b5708151
Source dataset
uspto-grants-1995_04
Patent number
US05405866

Reaction notes

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